Enantiomeric synthesis of L- (or 1S,2R,3S,5S)-bicarbocyclic[3.1.0] nucleosides

被引：7

作者：

Agrofoglio, LA ^{[1
]}

Demaison, C

Toupet, L

机构：

[1] Fac Sci, CNRS, ICOA, F-45100 Orleans, France

[2] Univ Rennes 1, Grp Mat Condensee & Mat, CNRS, F-35042 Rennes, France

来源：

TETRAHEDRON | 1999年 / 55卷 / 26期

关键词：

D O I：

10.1016/S0040-4020(99)00424-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of L- (or 1S,2R,3S,5S)-bicarbocyclic nucleosides (8-15) has been accomplished. The key intermediate 3 was synthesized in two steps from the known chiral compound 1 through a stereoselective cyclopropanation under Furukawa conditions and its X-ray structure has been determined. The derivative 4 was utilized to obtain thymine derivative (8). Amine exocyclic pyrimidine (9-12) and purine (13-15) bicarbocyclic L-nucleosides were obtained from the (IS,2R,3S,5S)-2-(3-aminobicyclo[3.1.0]hex-2-yl)ethanol (7). (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：8075 / 8082

页数：8